Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/26—Processing photosensitive materials; Apparatus therefor
  • G03F7/30—Imagewise removal using liquid means
  • G03F7/32—Liquid compositions therefor, e.g. developers
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D9/00—Chemical paint or ink removers
  • C09D9/005—Chemical paint or ink removers containing organic solvents
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/16—Coating processes; Apparatus therefor
  • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/26—Processing photosensitive materials; Apparatus therefor
  • G03F7/42—Stripping or agents therefor
  • G03F7/422—Stripping or agents therefor using liquids only
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters

Definitions

• the present invention relates to a photosensitive composition remover.
• the present invention removes the uncured photosensitive composition film on the peripheral part, the edge part or the back part of the substrate in the step of forming the photosensitive composition film on a glass substrate or a semiconductor wafer.
• it relates to a removal liquid for removing the uncured photosensitive composition adhering to the surface of the device member.
• the photosensitive composition removing liquid of the present invention is a process for forming a photosensitive composition film on a substrate in the manufacture of color fills used in liquid crystals, organic ELs, and image sensors, in particular.
• Useful for removal of photosensitive composition film containing uncured pigment remaining on the surface or back surface, or removal of photosensitive composition containing uncured pigment adhered to the surface of equipment members and instruments. is there. Background art
• pigment dispersion method As a pattern formation method for RGB or resin black matrix in the production of color fills used in liquid crystal, organic EL, image sensors, etc., pigment dispersion method, dyeing method, printing method, electrodeposition method, etc. are used.
• the pigment dispersion method is a method of patterning each color by photolithography using a photosensitive composition containing a pigment, and is preferable for producing a color filter because a stable colored film can be obtained. It is a suitable method.
• a step of coating a photosensitive composition containing a pigment on the substrate is included.
• the coating method includes spin coating and slipping. Methods such as coat coating, wire bar coating, roll coating, dip coating, spray coating or a combination thereof are known.
• the photosensitive composition When spin coating is performed, the photosensitive composition is usually used to remove the photosensitive composition adhering to the peripheral portion of the substrate after the photosensitive composition coating, the rising portion of the photosensitive composition film on the edge portion, and the back surface. A rinsing process with a material removal solution, so-called edge rinsing, knock rinsing is performed. Further, in spin coating, a photosensitive composition removing process using a photosensitive composition removing liquid is also performed in a process of removing the photosensitive composition scattered in the cup, that is, a so-called coupling.
• the photosensitive composition coating process in color filter production includes coating of the photosensitive composition by a slit coat method, coating using a wire bar, and coating by a roll coater.
• a slit coat method coating using a wire bar
• a roll coater coating by a roll coater
• a photosensitive composition containing a pigment used for producing a color filter that is,
• the color resist used for RGB formation and the black resist used for resin black matrix formation have pigment components in the substrate and equipment. It tends to remain on the surface, and even a slight amount of these may cause foreign matter, resulting in an increase in the defective rate of color filter manufacturing, or a change in color purity or a decrease in contrast of the color filter.
• glycol ether, its ester, or a mixture thereof is often used as a photosensitive composition remover (for example, Japanese Examined Patent Publication No.
• the object of the present invention is to remove a photosensitive composition having excellent photosensitive composition removal performance. It is to provide a effluent.
• the photosensitive composition film containing the pigment remaining on the peripheral portion, edge portion or back surface portion of the substrate Or a removal liquid effective for removing photosensitive compositions containing pigment adhering to the surface of an apparatus member or instrument.
• alkylene glycol monoalkyl ethers are component 1
• aromatic hydrocarbons are component 2
• alkylene diol monoalkyl ether carboxylic acid esters alkoxy force rubonic acid esters, alicyclic ketones.
• At least one solvent selected from the group consisting of alcohols and acetates is sometimes referred to as Component 3.
• the inventors of the present invention have made extensive studies to solve the above problems. As a result, it has been found that the use of a removing liquid having a specific composition improves the cleaning and removing properties of the pigment-containing photosensitive composition, and the present invention has been completed.
• this invention consists of the following matters, for example.
• a photosensitive composition removing liquid comprising:
• a photosensitive composition removing liquid comprising:
• a photosensitive composition removing liquid comprising:
• a photosensitive composition removing liquid comprising:
• Alkylene glycol monoalkyl ethers include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, Propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3 — methoxybutanol and 3 —
• the photosensitive composition removing liquid as described in any one of [1] to [5] above, wherein the liquid composition is at least one selected from the group consisting of methyl-3-methoxybutanol.
• Alkylene glycol monoalkyl ether carboxylic acid esters include propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, 3 — methoxybutyl acetate and 3 —methyl 3 —
• the alkoxycarboxylic acid ester is at least one selected from the group consisting of methyl 3-methoxypropionate and ethyl 3-ethoxypropionate [2], [3], The photosensitive composition remover according to [5] or [6].
• the acetic acid ester is at least one selected from the group consisting of ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, n-amyl acetate, isoamyl acetate and sec-amyl acetate.
• the photosensitive composition removing liquid according to any one of claims 2 and 4-6.
• the photosensitive composition removing liquid of the present invention remains on the periphery, the edge, or the back of the substrate in the step of forming a photosensitive composition film on the substrate in the production of liquid crystals, organic EL, image sensors, and the like. It can be effectively used to remove the photosensitive composition film containing the pigment to be removed, or to remove the photosensitive composition containing the pigment adhered to the surface of the device member
• the photosensitive composition removing liquid of the present invention is used for removing a photosensitive composition containing a pigment, and contains an alkylene glycol monoalkyl ether (component 1) and an aromatic hydrocarbon (component 2). To do.
• the alkylene glycol monoalkyl ethers (component 1) used in the present invention are suitably used as the main component of the photosensitive composition removing liquid because the solubility of the resin component contained in the photosensitive composition is high.
• the Specific examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono n-propyl ether, ethylene glycol isopropyl ether, Tilleng U Cole Mono n —Butelle ether, Jetylene glycol monomethyl ether, Diethylene glycol monoethyl ether, Jetylene glycol monopropyl ether, Diethylene glycol mono n-butyl ether, Propylene glycol monomethyl ether, P ⁇ Pyreneglycol monoethyl ether, Propylene glycol monopropyl ether, Propylene glycol mono_n —Butyl ether, Dipropylene glycol monomethyl ether, ⁇ Propylene glycol monomethyl ether, 3—Methoxyb alcohol , 3-methyl-3-methoxyb alcohol, and the like, but the present invention is not limited thereto.
• ethylene glycol monomethyl ether ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether
• Dipropylene glycol monomethyl ether, 3 — methoxybutanol, 3 — methyl-3-methyloxybutanol is preferred, and propylene glycol monomethyl ether, 3 — methoxybutanol, 3 — Methyl-3-methylbutanol is particularly preferred because of the high solubility of the photosensitive composition, the availability, and safety.
• Component 2 of the present invention is preferably an aromatic hydrocarbon substituted with an alkyl group, and examples thereof include alkylbenzenes and alkylnaphthalenes.
• the alkyl group may be linear or branched, or two or more groups may be linked to form a cyclic structure.
• the aromatic hydrocarbon preferably has 9 or more carbon atoms, preferably 12 or less. More preferable.
• component 2 examples include 1, 2, 3—trimethylbenzene, 1,2,4—trimethylbenzene, 1,3,5—trimethylbenzene, 1—ethyl-2-benzene, 1 1-ethyl-3-ethylbenzene, 1-ethylbenzene 4-methylbenzene, n-propylbenzene, cumene, n-butylbenzene, sec-butylbenzene, iso-butylbenzene, 1, 2, 3, 4, 4-tetramethylbenze 1, 2, 3, 5—tetramethylbenzene, 1,2,4,5—tetramethylbenzene, 1,2-dimethyl-3-ethylbenzene, 1,2-dimethyl-4 monoethylbenzene, 1, 3 —Dimethyl-2-ethylbenzene, 1,3 —Dimethyl-4 monoethylbenzene, 1, 3 — Dimethyl-5 —ethylbenzene, 1,4 monodimethyl-2 _ethylbenzene,
• aromatic hydrocarbons may be contained alone in the photosensitive composition removing solution, or may be contained in a combination of two or more. Among these, the boiling point is 1550 to 2500.
• Alkylbenzenes are preferred because they have high removal performance of the photosensitive composition, in particular, high removal performance of the photosensitive composition containing the pigment, and further have a drying property suitable for removal of the photosensitive composition.
• alkylbenzenes are alkylbenzenes having 9 or 10 carbon atoms, such as 1, 2, 3—trimethylbenzene, 1, 2, 4_trimethylbenzene, 1, 3, 5 _ trimethylbenzene, 1 _ethyl _ 2 _ methylbenzene, 1 — ethyl— 3 — methylbenzene, 1 — ethyl _ 4— methylbenzene, n-propylbenzene, cumene, n-butylbenzene, sec — Butylbenzene, iso-butylbenzene, 1, 2, 3, 4—tetramethylbenzene, 1, 2, 3, 3, 5-tetramethylbenzene, 1, 2, 4, 5-tetramethylbenzene, 1, 2-Dimethyl-3-ethyl benzene, 1,2-Dimethyl-4-ethyl benzene, 1,3-Dimethyl-2-ethyl benzene, 1,3-dimethyl-4-
• the aromatic hydrocarbon may be prepared by any method, Solvent naphtha with a high aromatic component ratio, for example, use of an alkylbenzene-based mixed solvent centered on 9 carbon atoms is effective, and the trade name Cielsol A (trademark: manufactured by Shell Chemical Co., Ltd.
• Preferred ratios of Component 1 and Component 2 contained in the photosensitive composition removing solution of the present invention are Component 1 force 95 to 70% by mass, and Component 2 is 5 to 30% by mass.
• component 1 and component 2 of the photosensitive composition of the present invention are in the above range, the solubility of the resin component contained in the photosensitive composition and the pigment content Scatter removability is good.
• the photosensitive composition removing liquid of the present invention includes alkylene glycol monoalkyl ether carboxylic acid esters, alkoxy carboxylic acids. At least one solvent (component 3) selected from esters, alicyclic ketones, and acetic acid esters can be contained.
• Component 3 that can be contained in the photosensitive composition removing liquid of the present invention is the solubility of the photosensitive composition by adjusting the photosensitive composition removing liquid to a polarity more suitable for the removal of the photosensitive composition. It is effective in that the removal rate of the photosensitive composition can be increased by reducing the viscosity without reducing the solubility of the photosensitive composition removing solution.
• Component 3 that can be used in the present invention include alkylene glycol monoalkyl ether carboxylic acid esters such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and ethylene glycol monoester.
• alkylene glycol monoalkyl ether carboxylic acid esters such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and ethylene glycol monoester.
• acetate esters ethyl acetate, n-propyl acetate, isopropyl acetate, ⁇ -butyl acetate, sec-butyl acetate, isobutyl acetate, amyl acetate, hexyl acetate, cyclohexyl acetate
• propylene glycol monomethyl ether acetate dipropylene glycol monomethyl ether acetate, 3-methylbutyl acetate, 3-methyl-3-methylpropyl ether
• alkylene glycol monoalkyl ether carboxylic acid ester, alkoxycarboxylic acid ester, alicyclic ketone, and acetic acid ester contained in the photosensitive composition removing solution of the present invention may be used alone or in combination. A combination of the above may also be used.
• the photosensitive composition removing liquid of the present invention contains component 1, component 2 and component 3, the preferred ratio of component 1, component 2 and component 3 is that component 1 is
• component 2 force S 5 to 30% by mass
• component 3 is 10 to 75% 3%.
• Component 3 is alkylene glycol monoalkyl ether carboxylic acid esters, alkoxy carboxylic acid esters, and alicyclic ketones.
• the more preferable ratio of Component 1, Component 2 and Component 3 is as follows: Component 1 force 85 to 20% by mass, Component 2 5 to 30% by mass, Component 3 10 to 7 to 5% by mass
• the more preferred ratio of Component 1, Component 2 and Component 3 is as follows: Component 1 is 85 to 40% by mass, Component 2 is 5 to 30% by mass, and Component 3 is 10 to 45% by mass.
• the colored photosensitive composition to which the removing liquid of the present invention can be applied is a colored photosensitive composition containing a pigment, which is usually used in a color filter forming process for liquid crystals, organic EL, image sensors and the like.
• These colored photosensitive compositions are photosensitive compositions colored by containing a pigment, and generally contain a film-forming substance that can be developed with alkali, a photosensitive substance, and a pigment. .
• the film-forming substance contained in the colored photosensitive composition examples include acrylic resins, novolac resins, polyimide resins, and polyvinyl phenol resins.
• the present invention is particularly acrylic. Removal of a colored photosensitive composition containing a resin as a film-forming substance can be suitably used.
• the acrylic resin used as a film-forming substance is a polymer or copolymer having a molecular weight of about 1, 000 to 500, 000 that is soluble in alkali, and contains a carboxyl group-containing ethylene. Copolymers of the polymerizable unsaturated monomer and other ethylenically unsaturated monomers are preferably used.
• the photosensitive material contained in the colored photosensitive composition includes hexaryl biimidazole when acrylic resin is used as a film-forming material.
• any pigment that is usually used in the production of power filter can be used without any problem.
• Organics such as black, yellow, red, blue, and green can be used.
• Specific examples of pigments that can be used alone or as a mixture of inorganic pigments include: Kiichi Bon Black, Acetylene Black, Lamp Black, Kiichi Bonn Nanotube, Graphite, Iron Black, Iron Oxide Black Pigment, Anilin Black, Sheanin Black, Titanium Black, C.I. Big Men ⁇ Yellow 1 20, 24, 8 3, 8 6, 9 3, 1 0 9, 1 1 0, 1 1 1
• the colored photosensitive composition may further contain an ethylenically unsaturated monomer in addition to the film-forming substance, the light-sensitive substance and the pigment.
• An ethylenically unsaturated monomer is a compound that polymerizes with radicals generated from a photopolymerization initiator upon irradiation with actinic rays.
• the colored photosensitive composition to which the photosensitive composition removing liquid of the present invention is applied includes an organic solvent, a pigment dispersant, an adhesion improver, and revealin.
• An adhesive, a development improver, an antioxidant, a thermal polymerization inhibitor and the like may be appropriately blended.
• the photosensitive composition decontamination solution of the present invention can be applied to the removal of a colored photosensitive composition that has been applied to or adhered to an object to be cleaned, and in particular, the removal of a colored photosensitive composition prior to photosensitivity. Can be suitably used.
• the colored photosensitive composition may be in a state where a solvent is contained, or may be in a state after the solvent is volatilized.
• a method for removing the colored photosensitive composition a method of removing the cleaning liquid by spraying the cleaning liquid from a nozzle or the like in a rod shape, droplet shape or mist shape on the object to be cleaned, which has been coated or adhered, Examples thereof include a method of immersing an object to be cleaned, to which a colored photosensitive composition is attached, in the removal solution of the invention.
• the photosensitive composition removing liquid of the present invention adheres to the peripheral portion, the edge portion, or the back surface portion of the substrate in the color photosensitive composition coating process for producing color filters used in liquid crystals, organic EL, image sensors and the like. It can be suitably used for removing unnecessary uncured colored photosensitive composition that has been deposited, or removing unnecessary uncured colored photosensitive composition that has adhered to part or all of the coating apparatus.
• the photosensitive composition removing liquid of the present invention removes the uncured colored photosensitive composition from the periphery, the edge, or the back of the substrate when the colored photosensitive composition is applied onto the substrate by spin coating. It can also be suitably used as a so-called edge rinse or back rinse, or a so-called coupling that removes the colored photosensitive composition scattered in the cup during spin coating.
• a slit coating method, a wire bar coating method, or a roll is used as a method of applying a colored photosensitive composition on a substrate.
• the coating method is known, when removing uncured colored photosensitive composition adhering to the surface of the applicator, such as slit nozzles, wire bars, and printing plates, The photosensitive composition removing liquid of the present invention is preferably used.
• Another embodiment of the present invention provides a substrate from which the uncured photosensitive composition has been removed by the above method using the photosensitive composition removing liquid, or a liquid, an organic EL, an image sensor, or the like. And the color fill obtained with this device.
• the detergency was evaluated in the following three stages by visual observation of the dissolution state of the photosensitive coloring composition after immersion in the removal solution for 3 minutes.
• the acrylic copolymer thus obtained had a solid content concentration of 22.1% by mass, an acid value of 9 2 mg KO HZ g, and a polystyrene-equivalent weight average molecular weight of 2 2, 0 measured by GPC. 0 0.
• Photosensitive Coloring Composition A Preparation of Black Photosensitive Coloring Composition
• Acrylic copolymer obtained in Preparation Example 1 30.0 parts by mass (solid content 6.6 parts by mass), EGA 5 0 parts by mass, Florene DOPA-3 3 (Trademark: Dispersant solid concentration 30% by mass) Kyoeisha Chemical Co., Ltd. 3. 3 parts by mass, Special B lack 4 (Dedasa Carbon Black) 6.6 parts by mass
• a black colored composition having a solid content concentration of 18.0% by mass was obtained.
• the black colored composition thus obtained was further added to 100 parts by mass of dipentaaldehyde hexitol hexylate 4.4 parts by mass, 2 — (4-methoxyphenyl) 1, 4, 6 _bis (Trichloromethyl) 1 s— ⁇ riazine 2.2 parts by mass and 5 parts by mass of EGA 2 were added and stirred sufficiently to obtain a photosensitive coloring composition A.
• Photosensitive Coloring Composition B Preparation of Green Photosensitive Coloring Composition
• Acrylic copolymer obtained in Preparation Example 1 30.0 parts by mass (solid content 6.6 parts by mass), EGA 5 0 parts by mass, Florene DOPA-3 3 (Trademark: Dispersant solid concentration 30% by mass, manufactured by Kyoeisha Chemical Co., Ltd.) 3. 3 parts by mass, 6.6 parts by mass of Pigment Green 3 6 After that, I left it for 1cm. Further, after stirring for 1 hour, it was passed through a three-roll mill (Model R III-1 RM-2 manufactured by Kodaira Seisakusho Co., Ltd.) four times. To adjust the concentration by adding EGA to the obtained green ink As a result, a green coloring composition having a solid content concentration of 18.0% by mass was obtained.
• the green colored composition thus obtained was further added to 100 parts by mass of dipentose erythritol hexacrylate.
• 4.4 parts by mass of 4,4′-bis (N, N-jetylamino) benzopheno 0.7 parts by mass, 2, 2 '— Bis (o _ black phenyl) 1, 4, 4', 5, 5 '— tetraphenyl _ 1, 2' — biimidazole 2.3 parts by mass, tri Methylolpropane trispropionate 3.8 parts by mass and 2 parts by mass of EGA 4 were added and stirred sufficiently to obtain a photosensitive coloring composition B.
• Photosensitive Coloring Composition C Preparation of Red Photosensitive Coloring Composition
• Acrylic copolymer obtained in Preparation Example 1 30.0 parts by mass (solid content 6.6 parts by mass), EGA 5 0 parts by weight, Floren DOPA-3 3 (Trademark: Dispersant solid content concentration 30% by mass, manufactured by Kyoeisha Chemical Co., Ltd.) 3. 3 parts by weight, 6.6 parts by weight of Pigment ed 1 7 7 , Left 1mm. Further, after stirring for 1 hour, the mixture was passed through a three-roll mill (Model R III — 1 RM-2 manufactured by Kodaira Manufacturing Co., Ltd.) four times.
• a red coloring composition having a solid content concentration of 18.0% by mass was obtained.
• a red coloring composition having a solid content concentration of 18.0% by mass was obtained.
• 4.4 parts by weight of dipentyl erthritol hexylate, Ilgacure 3 69 (manufactured by Ciba Specialty Chemicals) 3.0 parts by weight, Methylolpropane trisitol pionate 3.8 parts by mass and EGA 4 2 parts by mass were added and sufficiently stirred to obtain photosensitive coloring composition C.
• the present invention provides a photosensitive composition film containing a pigment remaining on the periphery, edge or back surface of the substrate

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• 2006
  • 2006-01-17 TW TW095101777A patent/TW200634448A/zh unknown
  • 2006-02-09 US US11/794,547 patent/US20080167210A1/en not_active Abandoned
  • 2006-02-09 KR KR1020077017143A patent/KR100944401B1/ko active IP Right Grant
  • 2006-02-09 CN CN2006800043693A patent/CN101116037B/zh active Active
  • 2006-02-09 EP EP06713814A patent/EP1847878B1/en not_active Not-in-force
  • 2006-02-09 WO PCT/JP2006/302673 patent/WO2006085678A1/ja active Application Filing

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